


Oral Presentation

by winecatsandpizza



Series: Office Matters [2]
Category: Supernatural
Genre: Alternate Universe - Office, Animated GIFs, Barebacking, Dirty Talk, Explicit Language, F/M, NSFW, NSFW Art, Office AU, Office Blow Jobs, Office Sex, Oral Fixation, Oral Sex, PORN gifs, Porn, Rough Oral Sex, Smut, Throat Fucking, nsfw gifs, unprotected sex
Language: English
Status: Completed
Published: 2018-11-25
Updated: 2018-11-25
Packaged: 2019-08-29 06:28:25
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,642
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16738828
Author URL: https://archiveofourown.org/users/winecatsandpizza/pseuds/winecatsandpizza
Summary: Jessy and Mr. Winchester have been seeing each other for a while now.  Jessy starts to let some of herself slip up to reveal just how much she enjoys him.





	Oral Presentation

**Author's Note:**

> This was originally posted to my Tumblr here: https://winecatsandpizza.tumblr.com/post/175764121993/oral-presentation

**  
  
  
**“Fuck, yes!” Jessy moaned as her boss, Mr. Winchester, slammed his throbbing cock into her sore pussy again.  It was a normal Tuesday morning.  She was splayed on his desk, legs wide while he stood in front of her forcing orgasm after sweet orgasm after her.  They have been doing this together ever since the first time months ago. **  
**

Jessy wasn’t sure if they were ‘dating’ per se, but she didn’t really care about that.  They had a conversation and they were only sleeping with each other and both had a clean bill of health.  Condoms were getting expensive and harder and harder to hide, so Jessy made sure that she always kept her birth control prescription updated and taken on time.

Jessy clinched around Dean’s cock as he thrust deeper inside of her.  “Gonna cum, Jessy.  Gonna fill you up with my cum, sweetheart,” Dean rasped.

“Yes, cum inside my little pussy, Daddy!” Jessy screamed as he spasmed inside of her.  Each spurt of his warm cum intensified her own orgasm taking over.  She didn’t even realize what she said until Dean slipped out of her and asked, “Daddy, huh?” with a smirk.

“What?” Jessy sat up while buttoning her white blouse back up.

“You called me Daddy.  I believe your exact words were, and I quote,  _‘Cum inside my little pussy, Daddy,’_  “ Dean smirked as he cleaned himself up and put himself back together.

Jessy blushed in embarrassment as she tried to explain, “Mr. Winchester, I’m so sorry. I-I’m not sure…”

He cut her off, “It’s okay, darlin’.  I don’t know if you noticed, but that made me cum even harder,” with a wink.  He placed a quick kiss on her cheek.

“I have a meeting to go to.  Finish cleaning up and I’ll be back in an hour.”

“Okay, no problem, Sir.”

Dean walked to the door of his office and turned around before he opened the door told her, “When I get back, I want you to be a good girl for Daddy, princess.”

* * *

 

Jessy could barely focus on her various tasks as she counted down the time until he returned.  She answered the calls that came in and scheduled the meeting for later in the month that needed to be set up with the different clients.  With ten minutes left, she went to go and get them a coffee.  This wasn’t supposed to be an intense meeting, but she knew, either way, a nice cup of coffee would make him happy.  

By the time she got back, he was already in his office with the door open.  She quickly entered and shut the door behind her.

“I brought you some coffee just the way you like it, Mr. Winchester,” Jessy offered with a smile.

“Thank you, sweetheart,” he smiled taking the coffee and setting it on his desk after taking a sip.  Jessy made her way around his desk and dropped to her knees and traced her hands up and down his muscular thighs.

“I have to make a few follow-up calls, sweetheart, and then you can show Daddy how good you are.”

“ _Or_ , I could do this,” Jessy counted as she settled herself in the spot under his desk and began to unbuckle his belt, “while you make your phone calls.”

“I knew I hired you for a reason, Jessy.  I love when you’re a naughty girl for Daddy.”

Jessy smiled as she freed his cock and balls from his pants and boxers.  He started dialing and as the phone call started, she began to lightly trace up and down his shaft with her finger and she cupped his balls with the other.

“Mmm, yeah. Just like that,” Dean murmured. “I said, yeah, just like that. That should work with what the client had in mind,” he corrected as he looked down at Jessy with a wicked smile on her face.

As Mr. Winchester’s conversation continued on, she traded her hand on his cock for her tongue. She slowly swirled her tongue around his dripping head and down the shaft before licking back up and starting over again.

“Yeah, I’ll write that up and send it over. Yeah, thanks, Goodbye,” Dean rushed and slammed down the phone.  

“You’re going to kill me if you keep teasing me like that, princess,” he warned.  Jessy looked up as innocently as she could as she swallowed as much length as she could.

“Hell yes, baby girl,” Dean hissed as Jessy kept a torturously slow pace. Dean placed a hand on the back of her head as he thrust his hips to match the pace.  “I love your mouth, princess. You are so-”  
  
Dean was cut off as there was a loud knock on the door.  He jerked back forcing Jessy off of him as he cleared his throat and invited the person in.

“Good afternoon, Mr. Winchester.  I’m Sam Wessen from IT.  You said you wanted to see me about upgrading some of our protocols?”

“Uh, yes. Yes.  Please, come in.  Sit down and make yourself comfortable, Sam.  Is it okay if I call you Sam?” Dean asked.

“Of course, Mr. Winchester.  I brought a few different proposals of how we could go about this if that is okay.” Sam offered.

Dean was thankful that he had chosen this sturdy, wooden desk that went all the way to the floor.  His first assistant wanted him to get a glass desk with exposed legs.   _That would have been a fucking disaster_. Dean thought to himself.

“I’ll just take a look through these real quick,” Dean announced as he took the files and started to review them.

Jessy was starting to get restless.  She could still see and smell the gorgeous cock in front of her.  She needed his cock and the added presence of another person only added to her excitement.   She silently moved closer and flicked the head of Dean’s cock with her warm tongue, which caused Dean to flinch.

“Are you okay, Mr. Winchester?” Sam asked concerned.

“Oh, yes,” Dean forced a smile, “Just a little leg spasm.   _Leg day_ ,” Dean chuckled.

“I understand,” Sam smiled while Jessy silently took more of her boss’ cock down her throat as she massaged his balls gently.  

Dean couldn’t read any of what was in front of him.  All of his focus was on keeping quietly as his little vixen was expertly servicing him.  Jessy started to go a little faster as she firmly placed her talented tongue on the underside of his cock.

“These look…fine.  Why don’t you…Why don’t you talk about these different options and explain them?  You’re the expert, after all, Sam,” Dean managed to choke out.

“Sure.  Okay, so this first option…” Sam started to go through his spiel and Dean tried to listen, but Jessy kept bringing him closer to exploding.  Jessy had grown to know the signs of when he was getting close.  She knew when to back off to prolong his impending orgasm.  Dean was not one to enjoy teasing and she knew she would get in trouble for what she was doing, but she was going to take full advantage of the situation.

“Option number two would entail…” Sam continued his pitch and only Jessy was listening.  Her multitasking skills were one of the reasons she was hired after all.  Jessy quietly released her mouth off of Dean’s cock and she felt him relax.  She let him breathe for a moment before she placed a delicate hand on his cock and started to stroke him as she licked his balls.  As she tried to be quiet there were still the slick noises as she stroked his throbbing cock.

Dean did his best to cover them by acknowledging what Sam was saying with words and sounds of agreement and understanding.  When Sam went into the third and last option, Jessy went back to sucking her boss’ cock.  She was more diligent this time. She added more suction and swirled her tongue as she bobbed quietly on his cock.  She knew she was getting him close and she had no plans on stopping.  

As soon as Sam was done he babbled out something about looking them over and calling him back later if he had questions.  Once he was gone and they were sure he was far enough away, Jessy let herself moan and loudly slobber on his cock.

“Fuck, princess,” he finally moaned out.  His mouth was dry and body tense.  Dean looked down to find Jessy focused on worshipping his cock as a hand was between her legs.  Breathlessly Jessy begged, “Please, Daddy.  Please cum down my throat.  I need you,” before she went back to work on his throbbing member.  

Dean placed his hand on her head as began to thrust deep into her throat.  Jessy relaxed her throat and let him take over.  Shortly, his gunts because louder and she felt his balls tighten as he released himself down her throat.  When the first ribbon hit her throat, she own pleasure overtook her as she came with Mr. Winchester.  

After they were done, she crawled out from under the desk, rubbing her sleepy legs lightly.

“Not that I didn’t enjoy that, but what the  _hell_ was that all about, sweetheart,” Dean asked earnestly. 

Jessy felt her cheeks redden as she shyly replied, “I  _kind of_  have an oral fixation.  I just can’t get enough of your beautiful cock, Mr. Winchester.  I love each vein, the thickness, the length, how soft your balls are…” She stopped herself from continuing once she saw Dean’s shocked face.  “I’m sorry,” Jessy stated barely above a whisper.

“Sweetheart, please do not  _ever_  be sorry for loving Daddy’s cock,” he replied with a loving wink.  “Let’s call it an early day and go back to my place so you can worship my _beautiful cock_ , darlin’.”


End file.
